CS257379B1 - Ethylene vinylacetate copolymere containing 2,2,6,6-tetramethyl-4-piperidylamino group and method of its preparation - Google Patents
Ethylene vinylacetate copolymere containing 2,2,6,6-tetramethyl-4-piperidylamino group and method of its preparation Download PDFInfo
- Publication number
- CS257379B1 CS257379B1 CS868573A CS857386A CS257379B1 CS 257379 B1 CS257379 B1 CS 257379B1 CS 868573 A CS868573 A CS 868573A CS 857386 A CS857386 A CS 857386A CS 257379 B1 CS257379 B1 CS 257379B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- tetramethyl
- preparation
- piperidylamino
- ethylene
- vinyl acetate
- Prior art date
Links
- -1 2,2,6,6-tetramethyl-4-piperidylamino group Chemical group 0.000 title claims description 9
- 239000005038 ethylene vinyl acetate Substances 0.000 title claims description 9
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229920001577 copolymer Polymers 0.000 title description 6
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 title 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- NRFOJVLXQQSBAQ-UHFFFAOYSA-N 3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]propanoic acid Chemical compound CC1(C)CC(NCCC(O)=O)CC(C)(C)N1 NRFOJVLXQQSBAQ-UHFFFAOYSA-N 0.000 claims 1
- 241000801924 Sena Species 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- XULIXFLCVXWHRF-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidine Chemical compound CN1C(C)(C)CCCC1(C)C XULIXFLCVXWHRF-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical class CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- GYZVPBNMZRMUOU-UHFFFAOYSA-N 2-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]propanoic acid Chemical compound OC(=O)C(C)NC1CC(C)(C)NC(C)(C)C1 GYZVPBNMZRMUOU-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
ČESKOSLOVENSKÁ SOCIALISTICKÁ REPUBLIKA (19) POPIS VYNÁLEZU K AUTORSKÉMU OSVEDČENIU 257379 (11) (Bl) (22) Přihlášené 24 11 86(21) (PV 8573-86.L) (51) Int. Cl.4 C 08 F 210/02 C 08 F 218/08 C 08 F 8/30 (40) Zverejnené 17 09 87 úRad pro vynálezy A OBJEVY (45) Vydané 15 12 88 (75)
Autor vynálezu MANASEK ZDENEK ing. CSc., PAJCHORTOVÁ ALŽBĚTA ing.,
VAŠŠOVÁ GABRIELA ing., VAŠŠ FRANTIŠEK RNDr., BRATISLAVA (54) Etylén-vinylacetátový kopolymér obsahujúci 2,2,6,6-tetrametyl-4--piperidylamínoskupiny a sposob jeho přípravy 1
Vynález sa týká etyléu-vinylacetátovéhokopolyméru obsahujúceho 2,2,6,6-tetrame-tyl-4-piperidylamíno skupiny a sposobu je-ho přípravy. Nízkomolekulové a polymérne zlúčeninyobsahujúce v svojej štruktúre sféricky tie-nené amínoskupiny sú účinné světelné sta-bilizátory užitkových polymérov [F. Gugu-mus, Developments in Polymer Stabilisa-tion-1, ed. G. Scott, Applied Science Publi-shers, London, 1979, kap. 8, F. E. Karrer,Makromol. Chem., 181, 595 (1980)].
Medzi zlúčeniny s vysokým stabilizačnýmefektom sa zaraďujú rožne deriváty 2,2,6,6--tetrametylpiperidínu, 1,2,2,6,6-pentametyl-piperidínu, 2,2,6,6-tetraalkylpiperazínu, 7,15-diazadispiroj 5,1,5,3 Jhexadekánu, 2,2,5,5-te-traalkylpyrolidínu. Sféricky tienené aminyúčinné inhibujú degradačné reakcie, ktoré 2 prebiehajú v· podmienkach prírodného star-nutia polymérov. Nevýhodou nízkomoleku-lových derivátov sféricky tienených amínovje ich prchavosť a vypieratefnosť, čo spóso-buje ich postupný úbytok z úžitkového po-lyméru už pri samotnom spracovaní, ale-bo pri působení různých látok s extrakč-ným účinkom. Přípravou kopolyméru podlá predmetuvynálezu sa eliminuje prchavosť a znižujeextrahovateťnosť tohto vysokomolekulovéhostabilizátora najma z polyolefínov. Zlúče-nina na báze kopolyméru, ktorá je predme-tom vynálezu nebola doteraz v odbornej li-teratúre popísaná.
Podstatou vynálezu je etylén-vinylacetá-tový kopolymér obsahujúci 2,2,6,6-tetrame-tyl-4-piperidylamíno skupiny vzorca I 257379 257379 kde R je CH,- . mx
CH
-CHI
O
I c-~o
I
Ct-íf-CHp-R m = 4 až 60, n = 2 až 4, p = 1 až 3, xmá hodnotu v rozmedzí od 40 do· 2.
Podstatou vynálezu je dalej spSsob pří-
pravy kopolyméru vzorca I vyznačujúcehosa tým, že sa na etylén-vinylacetátový ko-polymér vzorca II kde ~CHrCHr - - - — CH — CH. i i. rnx 0 1 O-C-CH^ rozmedzí od 4 nx (II) m = 4 až 60, n = 2 až 4, x má hodnotu v
kyseliny 3- (2,2,6,6-tetrametyl-4-piperldyl-amínojpropánovej vzorca III CH, CHa Η N y— NH~ CH?~ CH?· C. (lil) ch3 ch3
Claims (2)
1. Etyién-vinylacetátový kopolymér obsahujúci 2,2,6,6-tetrametyl-4-piperidylaroínoskupiny vzorca I - C/<- Cl·/,—(Z (Z -— · « -—- — CH- CH.—| (Z — ® * — — CH - Cli.— 1 C 0 0 i c = o I c=o I CH3 1 CH.-CH.~R mx (n-p) X íl) 257379 kde R je
ín --- 4 až 60, n = 2 až 4, p = 1 až 3,x má hodnotu v rozmedzí od 40 do 2.
2. Sposob přípravy zlúčeniny I podl'a bo- du 1, vyznačujúoi sa tým, že sa na etylén--vinylacetátový kopolymér vzorca II Γ τ ~ * -CH-Cl-L—£ iZ "— —, ch- CH I O 0=CCHA mx M * nx dl) kde ni -- 4 až 60, n — 2 až 4, x má hodnotu v rozmedzí od 40 do 2, posobí alkylesteromkyseliny 3- (2,2,6,6-tetrametyl-4-piperidylamí-nojpropánovej vzorca III
O XOR (lil) kde R1 je metylová alebo etylová skupina, vsuchom. toluéue alebo xylene pri teplote spatného toku v atmosféře dusíka za kata-lýzy amidu lítneho alebo zinesi amidu lítněho a amidu sodného. Severografia, n. p. závod 7, Most Sena 2,40 Kčs
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS868573A CS257379B1 (en) | 1986-11-24 | 1986-11-24 | Ethylene vinylacetate copolymere containing 2,2,6,6-tetramethyl-4-piperidylamino group and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS868573A CS257379B1 (en) | 1986-11-24 | 1986-11-24 | Ethylene vinylacetate copolymere containing 2,2,6,6-tetramethyl-4-piperidylamino group and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS857386A1 CS857386A1 (en) | 1987-09-17 |
| CS257379B1 true CS257379B1 (en) | 1988-04-15 |
Family
ID=5436467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS868573A CS257379B1 (en) | 1986-11-24 | 1986-11-24 | Ethylene vinylacetate copolymere containing 2,2,6,6-tetramethyl-4-piperidylamino group and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS257379B1 (cs) |
-
1986
- 1986-11-24 CS CS868573A patent/CS257379B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS857386A1 (en) | 1987-09-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4304882A (en) | Polymer from peroxy compounds containing acylating groups | |
| CA1282899C (en) | ISOPROPANOLAMINES AS CATALYST DEACTIVATORS IN SOLUTION PROCESS FOR POLYMERIZATION OF .alpha.-OLEFINS | |
| US4331586A (en) | Novel light stabilizers for polymers | |
| EP0042589B1 (en) | Norbornene polymers stabilized with hindered aromatic alcohols | |
| US3466261A (en) | Polyolefins stabilized by thioesters of antimonious acid | |
| US4769457A (en) | Glycoluril derivatives and their use as stabilizers for polymers | |
| US4057530A (en) | 2-Phenyl-indole derivatives and process for preparing the same | |
| Alvaradejo et al. | Maleimide end-functionalized poly (2-oxazoline) s by the functional initiator route: synthesis and (bio) conjugation | |
| US4356287A (en) | Novel polymeric light stabilizers for polymers | |
| JPH06234808A (ja) | 重合体の仕上法 | |
| EP0022501A1 (en) | Polycondensates of substituted piperidines and use thereof as stabilizers for polymers | |
| CS257379B1 (en) | Ethylene vinylacetate copolymere containing 2,2,6,6-tetramethyl-4-piperidylamino group and method of its preparation | |
| EP0426499B1 (en) | Polymeric additives | |
| Chmela et al. | Stabilising effect of monomers, homopolymers and copolymers of vinyl derivatives of sterically hindered amines on the photo-oxidation of polypropylene | |
| CA1336194C (en) | Siliconic stabilizer compounds for organic polymers, and process for their preparation | |
| JPH08259535A (ja) | 合成ポリマーを安定させるための組成物及び安定化方法 | |
| CS257380B1 (en) | Ethylene-vinylacetate copolymere containing 7,15-diaxadispiro(5,1,5,3)hexadecyle groups | |
| US4386177A (en) | Light stabilizers for polymers containing hindered piperidinyl-substituted 1,3,5 triazine groups | |
| Ferruti et al. | Synthesis and exchange reactions of some polymeric benzotriazolides | |
| US4370430A (en) | Hindered amine light stabilizers for polymers | |
| JPH02174775A (ja) | ２，６―ポリアルキルピペリジン置換ベンズイミダゾール―２―カルボン酸アニリド及びこれを使用する有機材料の安定化方法 | |
| US5281645A (en) | Benzophenones containing an ester functional group and their use in polymers | |
| SU429070A1 (ru) | СПОСОБ ПОЛУЧЕНИЯ БЕСЦВЕТНОГО СОПОЛИМЕРА .СТИРОЛА С АКРИЛОНИТРИЛОМ1Изобретение относитс к получению поли- стирольных пластических масс, в частности, к получению сополимеров стирола и акрилонит- рила, устойчивых к изменению цвета в услови х переработки в издели .Синтезируемые в промышленных масштабах сополимеры представл ют собой прозрачные, слегка желтоватые материалы. Непродолжительное нагревание их при 50—180°С, тем более при 200—220°С, св занное с переработкой материала, приводит к изменению цвета. Сополимер значительно желтеет и даже темнеет.Известен способ получени цветоустойчивых сополимеров путем термической полимеризации в атмосфере инертного газа смеси 80—60 вес. % стирола и 20—40 вес. % акри- лонитрила в присутствии 0,05^0,25 вес. % фосфорорганического соединени общей формулы1015где RI — алкил (Ci—€4); Ro — алкил (Ci—Сб); Rs — алкил (Ci—GS), арил или алк- арил. Этот способ позвол ет получить сополимеры, устойчивые к изменению цвета при температуре переработки в издели 200— 220°С в течение 30—40 мин.Цель изобретени — получение сополимеров, устойчивых к воздействию температур 200—220°С в течение продолжительного времени переработки в издели . Это достигаетс сополимеризацией в атмосфере инертного газа при повышенных температурах 80— 60 вес. % стирола с 20—40 вес. % акрилонит- рила в присутствии смеси, состо щей из 0,05—0,25 вес. % 2,4,6-триалкилфенола общей формулы2025ССН^)^СCICH^)^где R — алкил (Ci—€4),и фосфорорганического соединени общей 30 формулы | |
| CZ257691A3 (cs) | Kvapalné fotostabilizačné aditíva pre polyméry a spósob ich přípravy | |
| US4371695A (en) | Stabilizers for polymers and polymers stabilized thereby |